Patent GB-783728-A (GB)
Title: Improvements in the production of organic nitrogenous compounds
IPC: C07D203/26
Filed: 1955-06-24
Abstract: Compounds of the general formul  <FORM:0783728/IV (a)/1> <FORM:0783728/IV (a)/2> (wherein W, X, Y and Z represent hydrogen atoms or alkyl groups, and U and V each represent hydrogen or an alkyl group or jointly represent -(CH2)5-), and their ethers and esters, may be polymerized with the aid of polymerization catalysts, and may be co-polymerized with other polymerizable compounds.ALSO:The invention comprises compounds of the general formula <FORM:0783728/IV (a)/1> (wherein R represents hydrogen or an alkyl group), and the production of these and similar compounds by reacting a compound of the general formula <FORM:0783728/IV (a)/2> (wherein W, X, Y and Z each represent hydrogen or an alkyl group, and n is 1 (monoepoxides of conjugated diolefins) or is zero when W represents hydrogen (a  : b -unsaturated aldehydes)) with a compound of the general formula <FORM:0783728/IV (a)/3> (wherein U and V each represent hydrogen or an alkyl group or together represent -(CH2)5-), followed, if desired, by etherification or esterification of the hydroxy group thereby formed (e.g. by the action of ethylene oxide or ketenes, or of acid chlorides or anhydrides in the presence of an acid binding agent). The initial condensation may be effected in the presence or absence of solvents, dimeric products being obtained in the latter case under certain conditions of temperature and reaction time.  The products can add a second molecule of the imine at the double bond and can be quaternized, whilst their heterocyclic ring can be opened by the action of ring-splitting agents.  They are useful as intermediates for plastics, as auxiliaries in the textile, paper and leather industries, and in some cases as rubber vulcanization accelerators, as oxidation inhibitors or as medicaments for treating neoplastic diseases.  Examples describe the interaction (with formation of a monomeric product except where otherwise indicated) of: (1) ethyleneimine and butadiene monoxide in water below 25 DEG  C.; (2) the same compounds in the absence of any solvent at 30 DEG  C. (yielding a dimer and some trimer); (3) C-butylethyleneimine and butadiene monoxide in water at water-bath temperature; (4) acrolein and ethyleneimine in benzene below 25 DEG  C.; (5) methacrolein and ethyleneimine in benzene in the cold; (6) the product of (1) and 3 molecular proportions of ethylene oxide at 60 DEG  C.; (9) the product of (1) and about 10 molecular proportions of ethylene oxide in the presence of sodium methoxide at 65-70 DEG  C.; (8) the product of (1) and diketene in benzene in the cold; (9) the product of (1) and dimethylcarbamyl chloride in benzene in the presence of triethylamine in the cold; (10) butadiene monoxide and spirocyclohexane-ethyleneimine at 60 DEG  C.  Starting material. Spirocyclohexane-ethyleneimine is prepared by the action of alkali on 1-amino-1-chloromethylcyclohexane.ALSO:As vulcanization accelerators for rubber, and as oxidation inhibitors, may be employed compounds of the general formulae: <FORM:0783728/V/1> and <FORM:0783728/V/2> wherein W, X, Y and Z represent hydrogen atoms or alkyl groups, and U and V each represent hydrogen or an alkyl group or jointly represent -(CH2)5-, and their ethers and esters.ALSO:Pharmaceutical compositions, suitable for treating neoplastic conditions, e.g. by injection or by means of tablets, pills, pastes, ointments or suppositories, comprise, in conjunction with a carrier or diluent, at least one compound prepared by reacting an epoxide or aldehyde of the general formula <FORM:0783728/VI/1> (wherein W, X, Y and Z represent hydrogen atoms or alkyl groups, and n is 1, or may be zero when W is hydrogen) with an ethyleneimine compound of the general formula <FORM:0783728/VI/2> (wherein U and V each represent a hydrogen atom or an alkyl group or jointly represent -(CH2)5-), followed, if desired, by etherification or esterification of the hydroxy group so formed.  In an example, the compound of the formula <FORM:0783728/VI/3> (from butadiene monoxide and ethyleneimine) is made up in the following forms: (a) solutions in water, propylene glycol, polyethylene glycol or vegetable oils for peroral administration; (b) capsules containing solutions as in (a); (c) solutions in water, an isotomic solution of common salt or a camomile solution for administration by inhalation; (d) solutions in water, an isotonic solution of common salt or mixtures of water and polyethylene glycol for intravenous injection; (e) solutions in water, vegetable oils, propylene glycol or polyethylene glycol for subcutaneous or intramuscular injection, if desired with the addition of a local an sthetic.